Journal of the Chemical Society. Perkin transactions II p. 1659 - 1666 (1984)
Update date:2022-07-30
Topics:
Clemens, Anthony H.
Ridd, John H.
Sandall, John P. B.
The nitration of mesitylene by nitric acid in trifluoroacetic acid has been followed by 1H and 15N n.m.r. spectroscopy using H(15)NO3 (95-99percent 15N).With concentrations of mesitylene > 0.5 mol dm3, the direct nitration by the nitronium ion is accompanied by an autocatalytic reaction involving nitrous acid.The nitrous acid-catalysed process is inhibited by azide ions and can be made to predominate by the addition of nitrous acid.Nitration by the nitronium ion gives no nuclear polarisation in the product but the nitrous acid-catalysed reaction gives marked 15N nuclear polarisation: the 15N n.m.r. spectrum of nitromesitylene during reaction then appears in emission with a degree of enhancement that can exceed a factor of 200.This nuclear polarisation is attributed to the formation of a radical pair ArH+.NO2. by the diffusion together of the components.The side-products formed in the nitrous acid-catalysed process are consistent with reactions through ArH+..The direct nitration of mesytilene by the nitronium ion does not appear to involve this cation radical.
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